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KTIIYL  MALUKU.: ACID                          07
insoluble matter filtered off. The (liter is washed several times
with small quantities of ether, and the filtrate .shaken up with the
ether and separated. The filtrate is shaken up repeatedly with
fresh ether until the ester is completely separated, and the united
ethereal extracts freed from acid by shaking with a strong solu-
tion of sodium carbonate until the latter remains alkaline. The
ether extract is then separated, dehydrated with calcium chloride,
and the ether removed on the water-bath. The residual ester is
distilled under reduced pressure. Yield 45 -50 grains.
CILCLCOOIC I- KCN -:CI I,CN.('( X )K + KCl
CIUJN.COOK-|-2C,1I0OIM 2lI,S()t.....(MI,(C()()(:.,IIr))., I KIISOi
I NII,,IiS<)t.
rropcrties. —Colourless liquid ; b. p. 195" \ sl}- g1"- roott at rS'*
See Appendix, p. 256.
PUMP A NATION 23.
Ethyl Malonic Acid, C,II;>.(;il( ^[|
Conrad, Anna!en, 1880, 204, 134.
16    gnus, ethyl malonate
25       „    (32 c.c.) absolute alcohol
2'3     „    sodium
20       „    ethyl iodide.
Sodium ethylate is first, prepared by dissolving 2*3 grams
sodium in 25 grains alcohol, and the reaction completed, if
necessary, on the water-bath as described on p. 83. Whilst
the product is still slightly warm, in grams nudonic ester aio
added from a tap-funnel. The liquid remains clear at first, but
before the ester has all been added a white crystalline body
(sodium ethyl malonate) separates out, and soon the whole
solidifies. To the solid mass 20 grams ethyl iodide are slowly
added. The mass softens and, after continued shaking, com-
pletely liquefies with evolution of heat. The product is now
heated on the water-bath, when it becomes turbid from the
separation of sodium iodide in the form of a fine powder. After
one and a half hours the liquid ceases to be alkaline and the
reaction is complete. The alcohol is distilled off from a brine-
bath (water saturated with common sa,lt) On the addition of
COHEN'S ADV. p. u. c.                                                n